She was a political activist, worked for women's suffrage, social issues, to promote her father's call for the creation of the League of Nations, and was significant in the Massachusetts Democratic Party during the 1920s.

She was educated privately in Princeton, New Jersey at Miss Fine's School and at Goucher College in Baltimore, Maryland.

[2] In July 1913, four months after her father assumed the presidency, the Wilsons announced Jessie's engagement to Francis Bowes Sayre, Sr.[3] Her fiancé, a 1911 graduate of Harvard Law School, was the son of Robert Sayre, builder of the Lehigh Valley Railroad and organizer and general manager of the Bethlehem Iron Works.

[3] Upon their return from their honeymoon in Europe, they moved to Williamstown, Massachusetts, where her husband began his service as an assistant to the president of Williams College.

[citation needed] After World War I, the Sayres moved to Cambridge, Massachusetts, where Francis accepted a position on the Harvard Law School faculty.